1. Field of the Invention
The present invention relates to cetyl myristoleate (CMO). More particularly, the present invention relates to a commercial method for producing ambient-temperature-liquid cetyl myristoleate. The present invention further relates to the use and benefits of the ambient-temperature-liquid CMO product made by this commercial method.
2. General Background of the Invention
Cetyl myristoleate (CMO) is the ester produced by the reaction of cis-9-tetradecenoic acid (myristoleic acid) with 1-hexadecanol (cetyl alcohol). CMO was originally isolated as a natural product from a National Institutes of Health (NIH) albino mouse strain that was resistant was shown to have considerable anti-arthritic properties. Synthesized CMO demonstrated a similar protective effect. In the peer-reviewed journal Pharmacological Research, Hunter et. al show that in mice, pure CMO causes a significant reduction in the incidence and severity of arthritis (2). Furthermore, U.S. Pat. Nos. 4,049,824, 4,113,881, and 5,569,676 issued to Diehl relate to the use of CMO as an alleviator of arthritis (3, 4, 5).
Beginning in the early 1990s nutraceuticals containing CMO have been widely used for pain and inflammation relief in osteoarthritis. These CMO-containing nutraceuticals appear to be gaining market share perhaps partly as a result of comparison with some adverse physiological effects of the Cox-2 inhibitors such as Vioxx®, Bextra® and Celebrex® (registered trademarks of: Merck & Co., Whitehouse Station, N.J.; Pharmacia & Upjohn Company, North Peapack, N.J.; and G.D. Searle & Co., North Peapack, N.J., sold by prescription.)
Softgels (soft gelatin capsules) are becoming popular dosage forms for the administration of liquids, suspensions, pastes and dry powders in the dietary supplement industry. There are many dietary supplements in the softgel formulation. For example, GNC sells the vitamin supplement GNC A-Z in softgel capsule form, Nature Made provides, among others, Flaxseed oil, Conjugated Linoleic Acid (CLA), and Evening Primrose Oil in softgel formulations, and Nature's Bounty provides a Vitamin E supplement in softgel form. Softgels are not limited to dietary supplements. Pain relief, antiviral, laxative and many other medications can also be made or formulated into softgel capsules. Softgels have distinct advantages including, but not limited to; 1) ease of swallowing, 2) the ability to mask unpleasant odors and tastes, 3) the ability to have an elegant appearance with a wide choice of colors, 4) are easily dissolved in the digestive tract, and 5) have the possibility of enhanced bio-availability of the active ingredient.
Up to now, commercially available CMO has been made by the esterification of mixed fatty acids with cetyl alcohol. This has been done commercially in multi-ton quantities. Commercial cetyl esters of mixed myristic/myristoleic acids comprise a hard wax with a melting point of about 48° C. (˜120° F.). Unfortunately, this material cannot be injected directly into softgel capsules. Ambient-temperature liquid CMO has been made by Dr. Diehl in his work on the effect of CMO on arthritis in mice. However, in this work, CMO was synthesized by the esterification of highly pure myristoleic acid with cetyl alcohol. The projected cost of using such highly purified myristoleic acid to yield commercial quantities of ambient-temperature liquid CMO is prohibitive. For example, Dr. Diehl's work on the effect of CMO on arthritis in mice (1) synthesized cetyl myristoleate by the esterification of highly pure myristoleic acid with cetyl alcohol. The source of the myristoleic acid was listed as Nu-Chek Prep., Inc. Nu-Chek Prep., Inc. presently lists myristoleic acid at $80 for one gram, $375 for 5 grams or, projected, about $75,000/kilo, an entirely non-economic price. For at least these reasons, up until now a 40% active liquid CMO has not been available while being eminently desirable.
Currently, there is no economical method for producing CMO in a liquid form at ambient-temperatures in commercial quantities.